In today’s world, many of our health related issues such as muscularly pain, motion sickness, headaches and stomach aches can be relieved or even cured by taking a simple pill. Generally, these pills are made synthetically which is why pharmaceutical companies are prominent in today’s economy. Therefore, all matter is made of atoms in which it is artificially transformed into forms of pills to relieve almost any kind of pain. This is how we came up with the idea of choosing a specific drug which could be directly linked to an aspect that is touched upon in our course. We found a drug called Naproxen, which is also commonly known as Aleve.
The fact that Naproxen is actually a chiral drug is what got our attention at first. When Naproxen is used as Aleve, it is the S enantiomer of the drug. This enantiomer is mainly used to treat arthritis, hence relieve pain in the joints. To represent the soothing effect of S-Naproxen, we surrounded the spine in our artwork with a soothing color such as blue, which also explains the icicles on top of it. Having learnt that an enantiomer is a non-superimposable mirror image of a compound, we illustrated it in our art project. The line in the middle of the artwork represents a mirror. On the left side there’s the S-Naproxen molecule whereas on the right, its mirror image is drawn, which gives the R-Naproxen. Also, both left and right hands can be considered as enantiomers because they are also non-superimposable mirror images of themselves. In addition, the presence of letters shows that not everything can be enantiomers; some compounds such as meso compounds don’t have enantiomers because there’s an axe of symmetry. On the other hand, the R enantiomer doesn’t relieve anything. It actually causes liver poisoning, which explains the flames and the red color on the right side of the artwork. All the violent colors such as red, yellow and orange is representative of death, poisoning, or unstoppable pain.
This is why molecular shape is a crucial aspect in chemistry and plays a huge role in stereochemistry. In order for a compound to have an enantiomer, it has to have a chiral center. In the case of S-Naproxen, the 3D orientation of CH3 and CO2H at a chiral carbon decides its therapeutic properties. Changing the position of these two atoms, by taking its mirror image, transforms the compound into a liver toxin. Evidently, all atoms in this drug bond when electrons pair, which represents one of Atkins’s big ideas. If it weren’t for the electrons bonding, the two atoms, CH3 and CO2H, would not attach to the carbon atom, and consequently, would not form Naproxen.
Lastly, Naproxen goes through a synthesis to be produced. If the enantiomers are not properly separated once the synthesis is over, in this case R-Naproxen is the dangerous one, and is sold to the general public, many problems will occur. This was the case for thalidomide which caused defects on new born babies. The synthesis touches two of Atkins’s big ideas: there are barriers to reactions and there are only four types of reactions. When synthesizing Naproxen, many reactions such as substitution and addition, have to be done before getting the final product. Therefore, this involves bonds that are broken and formed over and over. In order to attain these reactions, we need a certain activation energy to break a bond and to reform it and thus surpass the barriers. In fact, the last step of the synthesis is the attack of a compound named N-alkylglucamine on the chiral carbon. Depending from where this compound attacks, from the top or from the bottom, the electrons from this compound will form a bond with the chiral carbon which will then lead to the S-Naproxen and R-Naproxen.
Works Cited
Stereochemistry." Khan Academy. N.p., 2014. Web. 06 Dec. 2014.
"Enantiopure Drug." Wikipedia. Wikimedia Foundation, 29 Nov. 2014. Web. 06 Dec. 2014.
Duggan, Kelsey C., and Matthew J. Walters. "Molecular Basis for Cyclooxygenase Inhibition by the Non-steroidal Anti-inflammatory Drug Naproxen." US National Library of Medicine. National Institutes of Health, 1 Sept. 2010. Web. 6 Dec. 2014. link.
Smith, Janice. Organic Chemistry, Fourth Edition. 159-178. New York, 2014. Print.